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Derek: [00:00:01] Jeff. Thanks so much for joining the show today, man.
Jeff: [00:00:05] Appreciate it, Derek. It’s always great to connect with former colleagues and I’ve been listening to your podcast for a long time, so I’m really happy you invited me to join.
Derek: [00:00:14] Yeah. Thanks, man. why don’t you kick us off by giving us a bit on. Your background. So we, you know, everyone knows we worked together and, I, I liked working with you. I thought you’re super sharp, but I think a lot of the people who are listening and the, you know, aspiring or recently promoted, you know, sales manager, might not exactly know how sales ops works from that perspective.
So maybe you can kick us off by talking about your background, how you ended up where you are, and then let’s move into. What should people know about sales ops?
Jeff: [00:00:49] Yeah. So at my current company, it’s called upkeep, we’re a, B to B SAS platform on a mobile app. And desktop for the maintenance and reliability spacover at that company, I am the head of revenue and growth operations encompassing and supporting marketing sales and customer success. So really think about it as qualified pipeline and engagement, all the way to sales, execution, to growth and continuity around upsells cross sells and renewals.
And so really getting a view of the entire business and serving as the right hand of, you know, a chief revenue officer, so to speak. And prior to joining. Upkeep. I bounced around quite a bit. I would like to consider my career into two halves, really think about it in two parts of an arc. The first half I was in technology consulting and sales, I worked in commercial real estate where I was a field rep to be all in all honesty and then moved into technical recruiting where I performed really well.
And. Went to business school and that this is where the intermission part comes in. And the second act of my current career has been supporting sales to some capacity, whether it was in finance, where at Google building out territory’s comp plan, it’s really understanding the economics of sales and how to enhance productivity.
Then from there, it’s really jumping into these midsize and startups and where I’m focused on sales operations, and we can go into what sales operations is and ever since then, that’s where I’ve. I made my bones and I love supporting driving customer value, which ultimately results in bringing revenue to the business.
Derek: [00:02:25] Got a little bit sales ops guy. Who’s actually carried a bag. what’d you say the product was that you were selling.
Jeff: [00:02:33] Well, I was in commercial real estate as a representing buyers and sellers. So, you know, your typical agent, it didn’t really work out that well, I’ll tell you that. Yeah. Much in real estate.
It’s, it’s, it’s a, it’s an old boys club, so to speak, people know each other with deep networks, I was walking in with no history or, you know, any pennies to behind my name. So, we can go into that. I obviously want to talk about the different types of, markets that you can sell into. Then secondly, I was a technical recruiter.
where I was working for companies looking to hire qualified candidates and particularly in tech technology, roles, assistants, administrators, systems, architects, Java developers. And that’s a really interesting whole industry because I don’t know. I know how to code at that point in time. Right. But I knew enough to ask the right questions about, you know, what are you looking for in your career?
What do you want to drive? And then trying to match that to companies who were looking for that profile from a culture fit, from a skill fit and from a kind of a general business acumen, you find that trifecta for, you know, the technical skills. I was able to match candidates and, and, and perform well there.
Derek: [00:03:37] Right. And that’s a role where you’re selling to both sides. You’re right. You’re selling candidates on why they should work with you or work with. or looking at a role and telling companies on why they should hire you to fill the role. It’s like the both ends of the desk.
Jeff: [00:03:51] So at that company, first started off on one side second, was able to contribute and start bringing in some business from the corporate bringing us job requisitions.
Definitely cool. but you know, when you’re in the recruiting business, there’s nothing more important than empathy and building relationships. And so when you’re wearing that bag and every day when I’m in sales ops or rev ops, and you think from that perspective, You know, what is the rep really care about?
What does the prospect really care about? And when you can put yourself in those shoes and you start to do, I think really well, right. And quite frankly, a lot of my ops peers start off from managing some sort of system or some sort of spreadsheet. And then from there it just kind of grows. But, there are very few that I think started off from actually selling it, getting on the phone and cold calling.
Derek: [00:04:37] Okay. That makes sense. You tell us about sales ops. What. You know, what stands out to you as being different that a newly promoted sales leader should know.
Jeff: [00:04:51] So sales ops is the team or function that partners with revenue leaders to merge strategy and execution. And so there’s a couple of tools in the belt and I go over these four key focus areas and then these four key pillars.
So these four key areas to focus on are going to be what I call peas in a pod. And they use pieces of this hokey little framework, but process. Enablement advisory. And systems. And then the print suppose that you go by are what I call these fast principles, where you want to build a rocket ship move quickly.
And that’s going to be focused alignment, simplicity, and teamwork. So if you can meet at the intersection. Of this four by four grid. I think you’re in a great place to position the business, to unlock real lessons in your go to market motion, whether developing and qualifying leads, whether that’s taking and those leads and peaking interest and moving to intent and engagement, and then passing that over to your AEs to help bring it to a qualified funnel because you see a scenario where you can work together and you’re successfully shepherding it through the sales motion.
And then on top of that, as opposed to LPs, which is, you know, let’s onboard the customer, let’s welcome them. Let’s check up on them and make sure that the value that we promised them in our sales cycle is coming true. And how do we get them to buy more buy often? And when they leave companies and go to somewhere else, they’re a champion for us.
Once again,
Derek: [00:06:17] I love both of those acronyms. You make me feel like I need more acronyms for the content that I create
Jeff: [00:06:23] too.
Derek: [00:06:25] I don’t know what that’s going to be
Jeff: [00:06:27] because I’m a forgetful person and having a mnemonic device or framework is something that you can always go back to. And so, yeah, it, I think it’s super helpful.
Derek: [00:06:39] Yeah. Sounds like it. So what, okay, so as you’re working within these sales, let’s say that you’re working at a company and somebody gets promoted from rep to sales leader. And they’re one of the early sales leaders. What are some things that, from the perspective of sales ops that that person can do maybe top two or three things in their first quarter, a couple of quarters to both work with sales as well, and to move the, build a business more towards scalability.
Jeff: [00:07:12] That’s an awesome question. Let me think about this. It’s funny cause you and I are freestyling here. We didn’t, we didn’t really prepare a whole lot of notes. So, so I think the first thing is, One, what does my team look like? capacity capability and coverage. So capacity is, do I have enough heads on my bench or, and do I have enough people behind in my candidate pipeline to make sure that I’m always going to be at full strength?
that’s capacity. Then there’s capability, which is taking a look at the skills of my team who is tenured, who is not tenured. Who’s the scientific rep and who’s the artistic rep and who’s who are the hybrids then there’s coverage. Where am I? Where are my leads coming from? If my inbound is enough and sufficient to hit my pipeline, let’s, let’s go.
If, if that’s not enough, how do I, you know, mine and harvest and hunt my patch to make sure that. We’re bringing in the necessary pipeline as well on an outbound basis. So that’s the first thing. The second thing is not just looking at your bench, but taking a look at, you know, what am I doing? That’s different from a sales rep to manager.
Cause what made you a successful sales rep doesn’t mean always make you a successful sales manager. Right? Oftentimes I have seen managers becoming super reps and. What you need to do is not show that you can close deals on behalf of your rep. And they’re going to learn through osmosis, but rather your, about hitting higher levels of batting averages across your team.
And what are those skills, right? And this is where you partner with ops and where you partner with enablement. What insights do I need from the business? Where can I carve productivity back in the form of fewer clicks or better systems? You know, what are the things that they, you need to prepare your team to be successful?
And then the third thing that I think you can do is, really sitting down with your sales ops group more often and really understanding, okay, what is a level one sales ops org in terms of paying down the process and technical debt versus a sales org that can bring insights to the business and put wind behind my sails, like high-octane to rocket fuel.
So, you know, those are the kind of the three things right off the bat right off the top of my head here that I think could be critical. Cool. And
can you talk a little more about technical debt when you, when you say that, what do you mean? And, how can a new leader help with that?
Technical debt is a term derived from, from programming.
Right? And so just imagine a software that needs to issue a quick fix, builds out a platform, sends it out and realize it’s pretty quickly that they’ve become the hottest app on the planet and their infrastructure beneath the service. Won’t. Be able to service the high level of traffic. and so they’re going to have to refactor their entire code base, very similar, in technologies as well as process.
If you have too much strategic, sorry, too much technical and process that you’ll actually burn into strategic debt as well. but let’s just talk about technical debt. Technical debt is. Essentially putting together a process or systems that solve for solution solve for paints the day, while forsaking the longer term picture.
Right? And so you, you you’re, you’re issuing a hot fix or, you know, a quick and dirty solution for today. but it actually leads you down the road to more pain. so let’s just look for example, from a sales rep perspective. Duplicate data. And in my system, I have too many leads, too many accounts that are the same.
And quite frankly, they’re inbounding and routing to different people. When in fact this lead is mine and I talked to this company and then his boss or her boss came in later as a secondary lead and got rid of the somebody else. How do you solve for a little minutia like that? That really creates real friction on the sales floor.
That to me is what I’m talking about. Technical debt.
Derek: [00:11:07] Right. Those situations suck up a tremendous amount of breath time. So you want them on the phone?
Jeff: [00:11:13] Absolutely. You want your seller selling and not having to file dispute tickets, fight with their managers, blame sales ops. You want to create a system that is well oiled and hopefully reduces as much friction as possible.
And what’s the best way for a new leader to work with a top team.
I think the first thing is, yeah, go ahead. That’s a good, so if I was a sales manager and the first thing that I needed to do was sitting with sales ops is one, you know, understanding what is my own role? How do I communicate my objectives to sales ops two?
Asking the question, how can we partner together? How can we partner? Well, three, where do we see the nature of our relationship going forward? in terms of what’s our communication style? How often should we be communicating? how do we go over opportunities and threats? And then how can I get on your radar to make sure that, We’re surfacing insights of the business that may not come through the data stream because sales ops will oftentimes look at the business in terms of the data that’s coming through.
But sometimes it’s, one-on-one the very conversational bits that come in through the everyday conversations that filter up to the management that sales ops will not see, or they will not hear. And so there are these other data points that I can honestly say I could use incorporate to refactor the business.
Derek: [00:12:39] Cool. So not a whole lot different from other departments communicate well with gum on the same page. I don’t like saying have a good relationship with, because I feel like that’s not specific enough, but like have open communication and figure out how, how each person likes to work or each team as they get bigger.
That’s a good reiteration.
Jeff: [00:13:04] Yeah, I’m not sure what to say. I think it’s the finding the relief, the finding a kind of rules of engagement of how to work together. and when can we agree to disagree or disagree to agree? You know, what are what’s, what’s the deal? It looked like. oftentimes when you’re not working harmoniously, we can start to devolve into this pointing finger salute a finger situation.
Derek: [00:13:30] Yeah, what’s a little bit off topic, but w what’s your, what’s your take? I guess conflict and healthy conflict can, can help the conflict exists between different departments.
Jeff: [00:13:46] Well, that’s a good question. Okay. I’ve heard this phrase and I think it came from Intel when I worked there a constructive confrontation.
Oh, okay. Right. And so. when you think about these resolutions, so there are these resolution tools that I like to use, and there’s a different tool for different situations. So for example, can we be challenging? That’s often my, my tool of choice is where I go in terms of my own nature is to be confrontational head on.
Then there’s the person who yields the person who says, look, this is not a fight. I’m going to fight today. Why don’t you just go with it? Then there is evasion evasion. Is I just, you’re going to duck this entirely. It’s not really worth my time. Then there’s the compromise. This is the, you know, one plus one equals 1.8 less than two, then there’s the win win one, one plus one equals five, you know, the super blossoming solution there.
And so you’ve got, gotta find the right resolution that works together. And so, you know, where we’re going through is figuring out what’s the right tool to pick at the same time. Right?
Okay,
Derek: [00:14:48] that makes sense. And it sounds to me like what that requires is everyone to be on the same page in terms of what happened next. Like we go through whatever this process is in order to get some results.
Jeff: [00:15:06] Yeah. Yeah. If you think about the constructive confrontation, right? Why people have cited, diversity is such an important element of building up the composition of your team, because when you’re looking at a problem or a problem set, for example, one person might fixate on a solution, but then the next person might come in and see it in an entirely different light.
And another person might come in and just say, let’s flip this upside down. Let’s let’s like a Worshack test. See what, see what falls out of it. And from those three angles, there’s those multiple angles. You might fall prey to paralysis analysis for sure. But you might also just might. Find a different way of solving that problem just because you incorporated different points of view.
And so that confrontation that we talked about, it doesn’t necessarily mean have to be antagonistic. It can just be I’m confronting your idea what a different way or a different method. And through this, because we have shared outcomes where we’re, we’re aligned to solving this problem together. Yeah.
Derek: [00:16:11] All right.
I like that a lot. alright, well, let’s, maybe get back a little bit more on topic. I love tangents though.
so thinking through solving problems like that, can you talk about maybe an example of how you worked with other sales leaders? And done some of this may, maybe outside the box or the type of problem solving.
Jeff: [00:16:37] And
Derek: [00:16:37] how about, how does that look in real life?
Jeff: [00:16:41] Well, let’s just take a classic example of deconstructing a sales process, right? So we walked through the sales process of, you know, Lee came in, varying levels of interest there. you either have to either ferment interest yourself or start qualifying depending on how.
What type of engagement you’re seeing from the County and the prospect, once it’s tossed over with a sufficient level of qualification from say your sales development function over to an account executive. At that point, you’re going through a discovery and you know, let’s face it. You know, SDRs are great at what they do, but different times they, they get varying levels of quality coming over the fence.
So the AAE has to be able to recognize that and say, okay, I see where I am. I’m going to go through a discovery as I’m going to discovery, I’m going through multiple why’s in the process so I can get to, why are you talking to us today? What is it about what you’re going through that compels you to you?
Take action. And let me see how I can find a solution to this. Set of problems you’re going through, where the solution that you’re you’re, you’re providing or you’re selling. Right. And that’s a very sales point of view of the funnel. now from sales office point of view, you know, I’m looking at it from the perspective of how many ops are coming through, how many leads did it take to get to those ops?
That gives me a conversion rate. Then I’m looking at trying to measure how many meetings or emails or calls are. Coming in between these different milestones. You know, that data actually is a Canary in the coal mine. It actually tells me, you know, point blank, what is, is sort of happening. And I’m developing hypotheses of the business and that’s where I’m partnering with sales managers.
Right. And starting to point out, Hey, take a look. I’ve seen that. Yeah. You know, our, our, our funnel or our a number of opportunities and these stages are sitting in that stage for far longer than they should be. Let me double click, triple click segment, the opportunities, try to get to a root cause of what’s happening.
It might very well be one particular app is kind of sandbagging their pipeline. two, maybe it’s the approach that they’re using to she’s out the discovery from the prospect that tells me that there is an opportunity for sales management or for enablement to come in. And so that’s where I think. Yeah.
You know, real descriptions of how to, you know, fine tune the revenue engine, so to speak, or the sales engine, you know, works really well between sales management, the rep and operations. Great.
Derek: [00:19:10] I love that those are like three very, truly different perspectives.
Jeff: [00:19:15] and that’s why, that’s why we worked together.
Cause we might see it from a different point of view.
Derek: [00:19:20] Cool. Anything else that you would want to share for you? If you could say anything or give any advice to somebody who’s either who’s expecting to be a sales leader, sip, maybe it just got promoted or they’re a few months away. What do you think it would be?
Jeff: [00:19:35] I think the number one thing that as a sales leader is to unlearn what I know. Right. Because. Every situation is different. Every role is different and come into it with an open mind and whatever I mean by that is what made someone a successful leader at another company, or what’s a successful sales rep now stepping into a leadership role for the first time.
It’s that? What made me successful? Isn’t always the same thing in my current state and to be open to that and figuring out how can and I get from where I am to where I want to be. I think that’s the most valuable thing, right? Because now you’re, you’re working on an even playing field.
Derek: [00:20:19] Cool. Well that man, well, it’s about time for us.
I want to thank you so much for coming on the show. And there was a lot of really
Jeff: [00:20:29] dense
Derek: [00:20:30] info that would have been extremely helpful for me when, you know, when I first got promoted. So thanks so much for coming on and sharing.
Jeff: [00:20:39] Yeah, appreciate it. Derek. I remember before I even joined patient Bob, you and I had connected on LinkedIn, which just happens to be a, kind of an omen from the skies that we were meant to like work together at some point.
Yeah. And we, and we
Derek: [00:20:54] got to for a while, I think that,
Jeff: [00:20:55] that
Derek: [00:20:56] coffee that we had on the promenade in Santa Monica, it still sticks out in my mind. You know, when you first joined.
Jeff: [00:21:05] Yeah. What a terrible way to spend your day in the, in the bright, near the beach in a nice latte.
Derek: [00:21:11] Ah, right. That’s a good, we got a good life out here, man.
Jeff: [00:21:15] Absolutely. Well, thanks again, Derek. I appreciate you having me on.
Derek: [00:21:18] Yeah. Thanks man.
